Intermolecular Twofold Carbopalladation/Cyclization Sequence to Access Chromans and Isochromans from Carbohydrates

Leibeling, Markus; Milde, Bastian; Kratzert, Daniel; Werz, Daniel B.

doi:10.1002/chem.201101917

Cited by 67 publications

(18 citation statements)

References 39 publications

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“…It was assumed that the multiple carbopalladation/cyclization sequence should give access to the fourfold-annulated ring system 13 in a single step. However, we knew that the domino process works much better in an intra- than in an intermolecular fashion [19]. Thus, we decided to employ a silyl ether moiety to connect both subunits 15 and 16 .…”

Section: Resultsmentioning

confidence: 99%

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

Leibeling¹,

Werz²

2013

Beilstein J. Org. Chem.

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A synthesis of anthracycline aglycone derivatives is described. The key step utilizes a powerful domino carbopalladation approach and subsequent ring closure. During this process two of the four rings of the anthracycline scaffold are formed. Differently substituted carbohydrates and dialkyne chains serve as versatile and simple starting materials for the reaction sequence. Diverse building blocks lead to a variety of different products and a broad range of structural diversity. 2194

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Section: Resultsmentioning

confidence: 99%

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

Leibeling¹,

Werz²

2013

Beilstein J. Org. Chem.

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“…Our recent interest in domino reactions starting with 2-brominated glycals [26–28] motivated us to investigate also the behaviour of peracetylated 2-bromogalactal 10 in Sonogashira–Hagihara reactions (Table 2). We found that 10 is much less reactive than 7 .…”

Section: Resultsmentioning

confidence: 99%

Sonogashira–Hagihara reactions of halogenated glycals

Koester¹,

Werz²

2012

Beilstein J. Org. Chem.

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SummaryHerein, we report on our findings of the Sonogashira–Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a substituent in position 2.

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“…To overcome the limitations of this intramolecular reaction with respect to the substitution pattern,a ni ntermolecularv ariant was developed. [69] However, al arge excesso ft he second alkyne was requiredf or it to be successful.…”

Section: Miscellaneousmentioning

confidence: 99%

“…Further deprotection of the hydroxy group in the product regenerated the carbohydrate core. To overcome the limitations of this intramolecular reaction with respect to the substitution pattern, an intermolecular variant was developed . However, a large excess of the second alkyne was required for it to be successful.…”

Section: Modification Of Sugarsmentioning

confidence: 99%

Homogeneous Catalysis: A Powerful Technology for the Modification of Important Biomolecules

Shelke

Yashmeen

Gholap

et al. 2018

Chemistry An Asian Journal

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Homogeneous catalysis plays an important and ubiquitous role in the synthesis of simple and complex molecules, including drug compounds, natural products, and agrochemicals. In recent years, the wide-reaching importance of homogeneous catalysis has made it an indispensable tool for the modification of biomolecules, such as carbohydrates (sugars), amino acids, peptides, nucleosides, nucleotides, and steroids. Such a synthetic strategy offers several advantages, which have led to the development of new molecules of biological relevance at a rapid rate relative to the number of available synthetic methods. Given the powerful nature of homogeneous catalysis in effecting these synthetic transformations, this Focus Review has been compiled to highlight these important developments.

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Intermolecular Twofold Carbopalladation/Cyclization Sequence to Access Chromans and Isochromans from Carbohydrates

Cited by 67 publications

References 39 publications

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

Sonogashira–Hagihara reactions of halogenated glycals

Homogeneous Catalysis: A Powerful Technology for the Modification of Important Biomolecules

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